@The_T I'm recalling a couple of stories.
A former student giving me a tour of a boutique machining house that makes one-off parts for everyone from the place down the street that makes fences for pig farms to federal contracts for classified parts. They had several pieces of machining equipment he was tasked to maintain because all of them ran end of life operating systems, all Windows of some sort, on which the software had been purposely EOLd by the manufacturer. The owner didn't want to replace a half million dollar piece of machining equipment because the software was old, so instead they relied on sneakernet and keeping internal IT staff that could maintain those old systems.
At one of my earliest IT jobs, in the early 2000s, we had one system locked in a physical cage, and when I asked what it was for, found out it was one machine that ran proprietary point of sale credit card processing for their one retail front in this facility. Their BANK, who provided the software, refused to update it and demanded they buy new hardware. So they kept a couple of WINDOWS 95 systems in a physical cage and only provided access to the IT director and accounting floor manager.
IMO these sorts of things should really be illegal. Maybe they could say something like businesses could be released of their liability by openly releasing the source for their apps and file formats, if customers want to take on the task of managing them. Some things are so hilariously expensive it'd be cheaper to hire a full time in house developer to maintain an app than EOL it and replace the devices it runs.